Synthesis, characterization and X-ray crystal structure of an allyloxo functionalized nonsymmetric nickel coordination complex based on N2O2 chelating ferrocenyl ligand

The synthesis of the new air and thermally stable orange neutral dinuclear iron–nickel unsymmetrical Schiff base complex, [8-(2-oxo,5-allyloxo-phenyl)-4,7-diaza-3-methyl-1-ferrocenyl-1-one-octa-1,3,7-trienato]nickel(II) (2), was achieved via the Williamson coupling reaction between the 2-oxo,5-hydroxyphenyl precursor 1 and allyl chloride in the presence of base. Complex 2 was isolated in 68% yield and characterized by IR, UV–Vis, 1H and 13C NMR spectroscopy, HRMS and authenticated by a single crystal X-ray diffraction analysis. The organometallic/inorganic hybrid complex 2 consists in a ferrocenyl fragment linked to a classical Werner-type complex made of an unsymmetrical quadridentate N2O2 Schiff base ligand with a pendant allyl ether functionality as a potential anchoring group. The Ni(II) center displays a square-planar geometry with the nitrogen and oxygen atoms occupying mutually trans positions. The structure of 2 · H2O shows that the water crystallization molecule interacts through two distinct intermolecular hydrogen bonds with the two oxygen atoms of the tetradentate N2O2 acyclic chelating ligand, forming in the solid state, a distorted six-membered ring.

Graphical abstractThe new air and thermally stable orange neutral dinuclear iron–nickel unsymmetrical Schiff base complex, Ni[(η5-C5H5)Fe(η5-C5H4)-C(O)CHC(CH3)NCH2CH2NCH-(2-O,5-OCH2CHCH2-C6H3)], in which the appended allyl ether functionality may serve as anchoring group, was synthesized by the Williamson coupling reaction and characterized by a X-ray crystal structure determination.Figure optionsDownload full-size imageDownload as PowerPoint slide